166376-67-6Relevant academic research and scientific papers
Asymmetric total syntheses of teretifolione B and methylteretifolione B via Diels-Alder reaction of optically active pyranobenzyne and substituted furans
Katakawa, Kazuaki,Kainuma, Mika,Suzuki, Katsuya,Tanaka, Saori,Kumamoto, Takuya
, p. 5063 - 5071 (2017)
We report the asymmetric total syntheses of teretifolione B and methylteretifolione B, which are benzochromenes originally isolated from Conospermum plants. The synthesis involves enzymatic asymmetric transesterification of racemic acetoxychromene and construction of the basic framework via Diels-Alder reaction of optically active pyranobenzyne and substituted furans. The absolute configuration of the chiral chromene was unambiguously determined by asymmetric total synthesis of teretifolione B and its characterization. The first asymmetric total synthesis of methylteretifolione B was achieved in a similar manner and its absolute configuration, for which direct proof has not been reported, was established.
Antiviral agents. I. Synthesis and antiviral evaluation of trimeric naphthoquinone analogues of conocurvone
Crosby, Ian T.,Rose, Mark L.,Collis, Maree P.,De Bruyn, Paula J.,Keep, Philip L. C.,Robertson, Alan D.
, p. 768 - 784 (2008/12/22)
Conocurvone, a novel natural product isolated from the endemic Australian shrub Conosperum sp. (Proteaceae), exhibits anti-HIV activity but is a highly lipophilic compound, which suggests that there may be problems with its aqueous solubility and bioavailability. A general and convenient synthesis of trimeric naphthoquinones using the condensation of 2-hydroxynaphthoquinones and 2,3-dihaloquinones is described. The application of this method to the synthesis of a series of simpler and less lipophilic trimeric naphthoquinone simple analogues of conocurvone is also reported together with their anti-HIV activity. CSIRO 2008.
